Dresses Over Jeans: A Retrospective : r Fauxmoi D&G 2000s Medium Blue Denim Corseted Lace Bra Dress The Kit Vintage Dress Over Pants? Why not.. When discussing fashion trends of the by Starryli Medium The early #2000s trend of wearing dresses over jeans was a popular #y2k era look, often featuring a long dress, like a babydoll or slip dress, layered over flared or skinny jeans. The early #2000s trend of wearing dresses over jeans was a popular #y2k era look, often featuring a long dress, like a babydoll or slip dress, layered over flared or skinny jeans.